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The Role of Conjugation in the Halogen−Lithium Exchange Selectivity: Lithiation of 4,6,7,9‐Tetrabromo‐1,3‐dimethyl‐2,3‐dihydro‐1H‐perimidine
Yakubenko, Artyom A.
, Tupikina, Elena Yu.
und Antonov, Alexander S.
(2023)
The Role of Conjugation in the Halogen−Lithium Exchange Selectivity: Lithiation of 4,6,7,9‐Tetrabromo‐1,3‐dimethyl‐2,3‐dihydro‐1H‐perimidine.
Chemistry – A European Journal.
Veröffentlichungsdatum dieses Volltextes: 26 Jul 2023 04:55
Artikel
DOI zum Zitieren dieses Dokuments: 10.5283/epub.54521
Zusammenfassung
The first case of successful suppression of the coordination of a lithium atom with a dialkylamino group by the effective conjugation of the latter with the aromatic core has been discovered. This effect controls regioselectivity of the bromine-lithium exchange in 4,6,7,9-tetrabromo-1,3-dimethyl-2,3-dihydro-1H-perimidine, which leads to products with the most effective conjugation. As a result, ...
The first case of successful suppression of the coordination of a lithium atom with a dialkylamino group by the effective conjugation of the latter with the aromatic core has been discovered. This effect controls regioselectivity of the bromine-lithium exchange in 4,6,7,9-tetrabromo-1,3-dimethyl-2,3-dihydro-1H-perimidine, which leads to products with the most effective conjugation. As a result, the product of this quadruple exchange demonstrates no tendency of the coordination of the NMe groups to neighboring lithium atoms despite the absence of steric restrictions. Experimental results are explained by means of quantum chemical calculations: geometry optimization, natural bond analysis and scans using the modredundant scheme.
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| Dokumentenart | Artikel | ||||
| Titel eines Journals oder einer Zeitschrift | Chemistry – A European Journal | ||||
| Verlag: | WILEY-V C H VERLAG GMBH | ||||
|---|---|---|---|---|---|
| Ort der Veröffentlichung: | WEINHEIM | ||||
| Datum | 1 Juni 2023 | ||||
| Institutionen | Chemie und Pharmazie > Institut für Organische Chemie | ||||
| Identifikationsnummer |
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| Stichwörter / Keywords | ; organolithiums; conjugation; coordination; regioselectivity; naphthalene | ||||
| Dewey-Dezimal-Klassifikation | 500 Naturwissenschaften und Mathematik > 540 Chemie | ||||
| Status | Veröffentlicht | ||||
| Begutachtet | Ja, diese Version wurde begutachtet | ||||
| An der Universität Regensburg entstanden | Zum Teil | ||||
| URN der UB Regensburg | urn:nbn:de:bvb:355-epub-545215 | ||||
| Dokumenten-ID | 54521 |
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